21-Bromo-3alpha-hydroxy-5beta-pregnan-20-one → 3alpha-Hydroxy-21-(pyrid-4-yloxy)-5beta-pregnan-20-one

HRID 582521노트

반응식

HRID 582521 반응식
Br[CH2:2][C:3](=[O:24])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C@@H:11]([CH2:12][C@H:13]([OH:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[OH:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1>C(N(CC)CC)C>[OH:23][C@@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:24])[CH2:2][O:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:12]1

참가 물질

4

반응물 2

HCID 8675425121-Bromo-3alpha-hydroxy-5beta-pregnan-20-oneHCID 178418642HCID 178418642, 화합물

생성물 1

HCID 213103243alpha-Hydroxy-21-(pyrid-4-yloxy)-5beta-pregnan-20-one수율 7.7%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

A solution of 21-bromo-3α-hydroxy-5β-pregnan-20-one (500 mg, 1.26 mmol), 4-hydroxypyridine (144 mg, 1.51 mmol), and triethyl amine (200 μL) in 10 mL of TBIF was heated under reflux for 4 h. The mixture was cooled to room temperature and partitioned between EtOAc and water. The organic layer was washed with sat. aq. NaCl, dried with MgSO4 and concentrated in vacuo. The crude residue was subjected to flash column chromatography. Elution with 50% acetone in CH2Cl2 yielded 3α-hydroxy-21-(pyrid-4-yloxy)-5β-pregnan-20-one (40 mg) as an oily solid; TLC Rf (acetone:CH2Cl2 1:1)=0.28.

후처리

  1. temperatureunder reflux for 4 h
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with sat. aq. NaCl
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. washElution with 50% acetone in CH2Cl2

출처 및 근거

ORD 기록
ord-debd6bf3650c4ffea209165729cffe37
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925630

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